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Houses Old Man Bay

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70 houses

Villa Caymanas: Caribbean Villa w/ Fabulous Snorkeling, Pool, & Panoramic

Old Man Bay house

4 bedrooms / 5 bathrooms / sleeps 8

“A perfect vacation!” The second spring time vacation we had at villa caymanas. When arriving, the view entering the front door blows me away each time I arrive. Property is well maintained and everything was super clean. Private ocean side back yard made it great for relaxing. House has everything you need and some extras. We drove most days to Rum Point Beach( 10 minute drive) to relax, great beach. Spent a few days never leaving the property as we grilled fish we bought from local fisherman at the docks. With the big group we had, the villa suited us perfectly as there was plenty of room inside and out. I liked best the privacy and location of the house, we enjoy getting away from it all and this place gave us that. Worst part about the house is saying good bye.

Responds fast! avg. 3 hours 5 minutes

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$630

Coral Cottage Pink: Cozy Old Man Bay Cottage with Infinity Pool Perfect for

Old Man Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 5 minutes

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$516

Cayman Sands: Secluded Beach Villa with Pool Atrium & Guest Cottage

Old Man Bay house

5 bedrooms / 5 bathrooms / sleeps 14

“A wonderful, relaxing paradise” I recently stayed at Cayman Sands with my husband, my in-laws, and our 2 young girls, ages 4 and 6. This home is everything we could have asked for - as gorgeous as the pictures, but even fresher (the larger bedrooms have been painted since the online photos). It was very spacious and clean, and the location was great for us - quite private (even with folks staying in the neighbouring home) but a quick drive to Rum Point, which is a great beach for families with young kids with its calm water, extended shallows and sandy bottom. We had the pool heated - well worth it - as our daughters spent long hours in the pool. The beach area is nice - although it is true the water in this area is more suited to snorkelling than swimming or wading, it was fine for us with the pool right there for the girls, and snorkelling convenient for us. There is washed up plastic garbage if you walk off the property down the beach - which is not the fault of the property managers or the island, but an unfortunate consequence of garbage mismanagement elsewhere and tides/storms washing debris onto the shore. The villa is well stocked with kitchen items, pool toys, beach towels, etc... We took a great glass-bottom boat tour from Rum Point with Red Sail Sports - to Stingray City and for a bit of snorkeling. This was a nice way to go as the boat is smaller, so fewer people and plenty of time for everyone to handle the stingrays and get photos and video without feeling rushed at all. Did some nice diving off Macabuca near the Turtle Farm - can rent gear right there. I would recommend this villa without hesitation, and hope to stay here again in the future. Cayman is a beautiful, safe island, and easy to explore since it's not too big. Jim Leavitt and his staff were wonderful to deal with throughout our searching for and booking of this villa, and provided great information to us before we arrived. The cleaning lady who came mid-week (Sharon) was friendly and efficient.

Responds fast! avg. 3 hours 5 minutes

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$859

Coral Cottage Yellow: A Scuba Diver's Paradise with Infinity Pool & Ocean Reef

Old Man Bay house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 3 hours 5 minutes

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$487

Coral Cottages: Two Oceanfront Villas with Infinity Pools in a Scuba Diver's

Old Man Bay house

6 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 3 hours 5 minutes

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$865

Villa Spirit

Old Man Bay house

3 bedrooms / 2 bathrooms / sleeps 6

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$440

Great rentals within 20 miles that match your search

SMB Area Private Villa From $995/wk ($100/ nite*)

West Bay house

2 bedrooms / 2 bathrooms / sleeps 6

“Cayman Relaxed” What a great place. Away from the congestion of seven mile beach. Two good restaurants, beach and a grocery store within walking distance. We made good use of the two outdoor hammocks. Nicely appointed kitchen although we just used it for breakfast every day. Six minutes from the governor's beach. 20 minutes from Georgetown. We plan on coming back.

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$205

Luxury Home near Rum Point w/ Beachfront Pool, Spectacular Views, # 1 Cream

North Side house

3 bedrooms / 3 bathrooms / sleeps 8

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$522

RUM POINT -Ocean Front Villa

Rum Point house

3 bedrooms / 2 bathrooms / sleeps 7

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$341

Ocean Paradise # 4 Green - Affordable Luxury Home w/ pool

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

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$682

Ocean Paradise # 3 Blue - Affordable Luxury Home w/ pool

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

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$523

Ocean Paradise # 1 Cream - Affordable Luxury Home w/ pool

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

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$523

Sandbar Beach Island House 11, steps from Rum Point, FREE kayaks, bicycles, WIFI

Rum Point house

2 bedrooms / 3 bathrooms / sleeps 6

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$427

2 BR 2 BA 7 Mile Beach Btwn WESTIN & RITZ, GROUND FLOOR

Seven Mile Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

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$410

Tranquil Bed and Breakfast Accommodation

Bodden Town house

1 bedroom / 1 bathroom / sleeps 2

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$114

Ocean Paradise # 2 Peach - Affordable Luxury Home w/ pool

Rum Point house

3 bedrooms / 3 bathrooms / sleeps 8

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$522

Very Spacious Ocean View 2 Bed 2 Bath - Unit #1

Bodden Town house

2 bedrooms / 2 bathrooms / sleeps 4

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$114

Luxurious beachfront, 2 bed, 2 bath, pool & tennis

Bodden Town house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 27 minutes

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$229

Beautiful White Sandy Beach. Specials: Stay 7 nights pay only for 6 nights

North Side house

3 bedrooms / 2 bathrooms / sleeps 6

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$452

Tiki House Grand Cayman, Seven Mile Beach Area

West Bay house

4 bedrooms / 2 bathrooms / sleeps 6

“Best girls' beach trip ever” This was my second time staying at Tiki House and the experience was wonderful both times. Everything one could possibly need in a vacation home is provided and just down the street is an enormous grocery store where one could buy all the fixings for any in-home meal. Especially nice is the lanai covered with bougainvillea. Great for morning coffee or afternoon cocktails. (There is even an outdoor shower for cleaning off after a day at the beach.) The location is excellent with the beach literally only a 45 second to 1 minute walk. Walking another 30 seconds brings you to a fabulous restaurant, Alfresco, which is great outdoor Italian and seafood dining (especially at sunset.) Being on the west side, the view of sunset is breathtaking.The entire 5 days I stayed were totally relaxing and part of that is due to the accommodations at Tiki House and its location.

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$458

Laguna Del Mar # 18

Seven Mile Beach house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 28 minutes

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$1,030

Laguna Del Mar #9

Seven Mile Beach house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 28 minutes

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$1,030

Laguna Del Mar # 1

Seven Mile Beach house

4 bedrooms / 4 bathrooms / sleeps 11

Responds fast! avg. 3 hours 28 minutes

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$1,030

Laguna Del Mar # 2

Seven Mile Beach house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$801

Laguna Del Mar # 15

Seven Mile Beach house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 3 hours 28 minutes

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Price per night from

$801

Laguna Del Mar # 5

Seven Mile Beach house

3 bedrooms / 3 bathrooms / sleeps 7

Responds fast! avg. 3 hours 28 minutes

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$801

Laguna Del Mar # 8

Seven Mile Beach house

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 3 hours 28 minutes

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$1,030

Regal Beach Club #114

Seven Mile Beach house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 28 minutes

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$458

Northside Grand Cayman Getaway w/ Private Beach!

Rum Point house

4 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 3 hours 38 minutes

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$490

Starboard Kai Beachfront Home with Great Beach Location at Rum Point, Cayman Kai

Rum Point house

2 bedrooms / 3 bathrooms / sleeps 4

“Paradise Found” This was our first time to Grand Cayman Island. We were very excited to go as a family for the first time to the Caribbean. We usually like to vacation at destinations that are not too “touristy” so we decided to stay away from the seven mile beach strip, since we heard that was very busy. We are so grateful that we found this wonderful townhome at Rum Point. Starboard Kai was very tastefully decorated, really clean and very well stocked. They even had a complimentary water cooler for us which were so helpful. They had three kayaks with life jackets, bikes (which we never got a chance to use), laundry in the unit (just make sure you bring your own HE laundry detergent), dvd player (I am not sure if we saw any dvds, but we hardly watched any TV since were had full days), coffee maker, spices, pool towels, beach toys. The only thing we needed was food, that’s how well stocked this place was. It was so nice to be right across from a Rum Point where our boys could play in the water, without worrying about waves. The location is superb, since you have the beach right in front of the condo and the beautiful bioluminescent bay in the back. It was so nice to lounge in the lanai and see the bay. From the living room and office you had nice views of the ocean of Rum Point. Many beautiful parrots, roosters and iguanas to see here, which was really neat! We did venture towards Seven mile beach and other areas of interest but wished we had just spent more time at our home base Starboard Kai. We checked out all the top beaches on the island and found our location to be #1. Janice the owner was a delight to work with; she really goes above and beyond to accommodate her guests. We also found Bob Wagner, the property manager very helpful as well. They truly excel in customer service and were very responsive to any issue we had. We loved going to the recommended restaurants. Loved our day at Sting Ray city, with Red Sail Sports which to sign up is right across the street and leaves from Rum Point’s pier. We really liked the blue iguana sanctuary nearby. We also have great memories of feeding the ‘Pirate’ Frigate birds at Tukka, a restaurant on the east end. Going to get sticky toffee pudding and seeing the Tarpons at Calypso Grill was fantastic as well. Would highly recommend this to others and have. When we got back we showed my friends and family and were amazed how beautiful everything was. Hoping to go back soon!

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$458

Tranquil Caribbean Beach Home

East End house

4 bedrooms / 4 bathrooms / sleeps 8

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$401

Relax at Coconut Bay!

West Bay house

3 bedrooms / 4 bathrooms / sleeps 7

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$344

Stunning and Luxurious Modern Villa with 7 Oceanfront Suites

Bodden Town house

7 bedrooms / 8 bathrooms / sleeps 20

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$2,729

Avocado Cottage: Boutique Oceanfront Micro-Resort 10 mins from Seven Mile Beach

West Bay house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 5 minutes

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Price per night from

$401

Cayman Dream: Rum Point Beach Bungalow with Pool for Oceanfront Living

Rum Point house

2 bedrooms / 2 bathrooms / sleeps 6

“Cayman Dream” We rented Cayman Dream in early June of 2013. We were very happy with the house. It's exactly as the pictures show. The kitchen is very well appointed and the grounds are kept very nicely. It's located in a nice quiet area with very little traffic. Our only complaint with the house was the phone/wifi. It was out for three of the six days that we were there and even after it had been fixed we had to constantly reset while we used it. With our children back in the states, we felt really out of touch. We truly enjoyed our stay and would recommend staying there.

Responds fast! avg. 3 hours 5 minutes

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$458

Conched Out: Island Chic Bungalow w/ Lush Tropical Landscaping,Pool & Backyard

North Side house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 5 minutes

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$315

KiToCay: Modern Beach House w/Over-the-Water Sun Deck & Private Beach Lot

North Side house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 5 minutes

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$453

Mango Cottage: 2-Bedroom Cottage on Oceanfront Micro-Resort 10 mins from Seven

West Bay house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 3 hours 5 minutes

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Price per night from

$401

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